DAN MCGINN: Welcome to the HBR IdeaCast. From Harvard Business Review, I’m Dan McGinn. I’m on the phone today with Scott Adams, creator of Dilbert. And the subject of the life’s work interview in our November magazine. Scott has a new book out entitled How to Fail at Everything and Still Win Big. Kind of the story of my life. Scott, thanks for joining us today.

SCOTT ADAMS: Thanks for having me.

DAN MCGINN: So, Scott, this new book is a memoir. Why did you write it?

SCOTT ADAMS: Well, when I was a kid, I grew up in a small town in upstate New York. And I didn’t really have a lot of role models who had been really successful. I mean, people had been successful in their jobs, but nobody had really broken out and done something important. And I always felt jealous of all those rich kids, the Harvard-bound types, who could look at their family and their friends, and they just got all kinds of advice, all kinds of useful tidbits, role models, that sort of thing.

And I thought, wouldn’t it be nice to write a book about how at least one person did it. I’m not suggesting that anything that I do would work for anyone else. But I think it’s useful to see people’s story, see what was your plan, what did you do, how did it turn out. So that was the genesis part.

DAN MCGINN: Before you were a cartoonist, you earned an MBA degree. What did it teach you?

SCOTT ADAMS: Well, Dilbert was one of the few success stories that came out of that era. It’s very unusual for a comic to break out. And I would say that, at least, half of that had to do with my business training. And the other half is just pure luck and timing, and being in the right place at the right time, which I also talk about at length in the book.

But just to give you a specific example, when Dilbert first came out, I didn’t really know what was working and what wasn’t, because I had no contact directly with the readers. And it doesn’t take a lot in the MBA program before you’re taught what seems obvious now, that you need to have a direct channel to your customers, and adjust your product based on their feedback. So I started putting my email address in the margins of the strip, way back in the dawn of the internet.

And I got just hundreds, sometimes thousands of messages a day and found out that there was a common theme. People loved it when Dilbert was in the office and they liked it a lot less when he was at home, or just hanging around. And Dilbert became an office-based comic. And that was really the change that made it all work. Now, since then, as it got bigger, just managing the Dilbert empire from anything from the contract negotiations to the calculating the cash flow for various business interests, almost every bit of education I got at Berkeley was useful.

DAN MCGINN: During the first five years you were writing Dilbert, you continued working full-time in corporate IT. Why did you do that?

SCOTT ADAMS: Well, in my case, I couldn’t quit my day job right away, because the comic started very slowly. And then, as I said, it wasn’t until I made it a workplace comic that it even had any potential. So the first few years was just necessity, but eventually, it turned out that I was getting so much material during my day job for the strip that instead of being twice as hard by having two jobs, it actually made both of them much easier.

So my day job didn’t bother me anymore, because I didn’t worry about getting fired so much. You know, at least i had a back up plan. And my cartooning job was almost ridiculously easy, because I was just transcribing my experiences that happened that day. So the two of them worked together to be effectively like one job.

DAN MCGINN: How much harder was it to find material once you left your job at Pacific Bell?

SCOTT ADAMS: It was a little harder. I still got tons of email from people suggesting things. And, unfortunately, the cubicle existence is a little like prison in the sense that you can imagine somebody getting out of prison after 30 years, and you say, do you still remember that? Do you have any vivid memories of that cell? you know, the memories don’t really die.

DAN MCGINN: At one point, Dilbert was published in 70 countries. How well does this material translate across cultures?

SCOTT ADAMS: Well, it seemed to work everywhere that there was some kind of a cubicle culture. And I’ll call it a Western business attitude or way of doing things. So it didn’t work as well in Japan, for example, where being insolent to management just seemed like something you wouldn’t do, whereas in Australia and Great Britain, for example, you would expect that the employees are going to be pretty cynical and they’re not going to hold their tongue that much, especially the engineers, who are a little bit less frightened of getting fired, because they’re highly employable.

DAN MCGINN: You launched the Dilbert website in 1995. Why were you thinking about a digital strategy so early?

SCOTT ADAMS: It’s funny to think back to those early days of the internet when people didn’t know how things were going to play out. But originally it was kind of a back door marketing plan, because it’s really hard to sell into newspapers. They usually have to fire a cartoonist to get a new one and they don’t like to do that, because people complain. So it’s hard to sway a manager.

And I thought if we can get people excited on the internet, we could gather letters from people who said, hey, I like this, and bunch them up, and hand them to the sales people. And they could take that into the editor and say, look, people already like this thing, so there’s no risk. And it turned out that’s exactly what happened. We just got hundreds and hundreds of positive emails. And the sales guys literally took them in and spread them out on the desks of the editors, who said, OK I get this. Let’s have that tomorrow.

DAN MCGINN: As a cartoonist, you sell your strips to newspapers. How early did you get a sense that the newspaper industry was in trouble and how do you try to shift your business model?

SCOTT ADAMS: You know what’s strange is that I predicted newspapers would only last five more years almost the day that I started cartooning? So I’ve been wrong on my five-year prediction every time so far. And even as newspapers shrunk, usually it was a city that two newspapers would go down to one, and Dilbert usually was a survivor, well, really, every time, was a survivor in the remaining newspaper.

So it turns out, I had no impact on revenue and just kept growing. So it’s actually at the largest number of newspaper customers it’s ever been at. But obviously, readership in general is declining.

DAN MCGINN: In your new book you list a whole series of business ventures that you started that failed– a frozen burrito company, two restaurants, computer programs, tennis gadgets– how did these failures change the way you think about management?

SCOTT ADAMS: In this case, the failures were all part of a larger strategy, which was trying one thing after another, they had the quality of if it worked– and they were all long shots– if it worked, they could grow forever. There was no upside camp. So that was always my strategy right out of college, I actually had a diary, which I still have, in which I’d mapped out my life strategy. And that was to build something using my creativity that could be reproduced easily and infinitely. And Dilbert was just the thing that worked. The other things you mentioned were kind of in that category, but they didn’t work.

DAN MCGINN: One of your employees once said, Scott should be shielded from tough decisions the way a crawling infant needs to be protected from household hazards. Is it true you’re not the world’s best manager?

SCOTT ADAMS: They were probably too kind. Yeah, there’s a tough balance being a manager. You can’t be too liked, and I like to be liked. So completely incapable as kind of a day-to-day manager, because I’m more interested in being liked than getting the job done. So yeah, I was largely incompetent at that and many other things I did.

But in the restaurant in particular, I’d gone into that to be a investor not a manager, and I ended up doing a little managing toward the end, just to see if I could make a difference, and it didn’t.

DAN MCGINN: How did your own experiences as a manager inform the cynical tone of Dilbert?

SCOTT ADAMS: My most basic belief about management is that it’s people flailing around, hoping that something lucky happens external to them that makes them look as if they did a great job. And all of my experiences of that type, which is if you looked at the things that failed, objectively, they weren’t worse ideas than the things that worked. And there was nothing about the execution, especially, that was the make or break, it was almost always the timing, the luck, the lightning struck.

And so I always manage my career to do enough things that if there’s enough lightning and I’m doing enough things, my odds of getting lucky are pretty good. And that’s my basic view of most management. You know, Eric Schmidt is worth how many billions of dollars because he hooked up with the Google guys and went to work every day. Maybe he’s the best manager in the world, but he kind of was a little bit lucky that he got that job.

DAN MCGINN: So you’re saying management really doesn’t matter?

SCOTT ADAMS: I think it’s certainly something you can do wrong. So avoiding doing it wrong is the big thing. And I think if you’re a bit of a psychopath or sociopath, I don’t know the exact definitions of those, you know, if you push people to think that you being happier, and you as the manager making more money, and you as the company making more money is more important than the employees’ own personal life and their health, then you’re a great manager. And you absolutely can do great things. And you’ll probably be able to reproduce that wherever you go.

So there’s a certain amount of evil that’s built into the system. It’s a creative evil. I mean, I’m very pro capitalism, because I don’t have a better idea that obviously works. But you’ve got to embrace that evil a little bit and you’ve got to understand that that’s part of the process, and that’s always been a problem for me.

DAN MCGINN: Do you really believe the Dilbert principle, the idea that the least competent people become bosses, because it’s the place where they can do the least harm?

SCOTT ADAMS: Well, at the time it was written, I was working at Pacific Bell. And they very much were doing that exact thing. So the people who were a little bit technical, but, really, they weren’t going to be inventing the next iPod or anything else, those people got moved to management, because, maybe, their bullshit skills were good, that was about it. And the people who were geniuses, the technology gurus, the people who were really going to make a difference, the last thing you want to do is ruin their productivity by moving them into management and making them order donuts and schedule meetings.

DAN MCGINN: Did you watch the TV show The Office? Either the British or the American versions of the TV show?

SCOTT ADAMS: I watched them both and love both of them, yeah.

DAN MCGINN: Did you think that they were drawing on Dilbert at all, or did you see their sensibility as somewhat different?

SCOTT ADAMS: 100% different. In fact, it’s kind of a weird psychological experiment why anybody would see them as similar in the first place. They’re, I guess, about incompetent bosses and bad employees, but it kind of ends there. Their shows were entirely character-based and about their love interest, and almost none of it was about anything that looked like work. Dilbert’s more about the strangeness of the power dynamic between managers and employees, and the ridiculousness and the absurdness of the management structure sometimes, and the craziness of the management fads.

DAN MCGINN: Have you sensed the lull in management fadism?

SCOTT ADAMS: Yeah, actually, if you were to plot it on a graph, you would find that the number of management books was increasing up to about the time that the Dilbert principle came out and said, I’m pretty sure every bit of this is bullshit. And so many people agreed with that, that I think it just became a little more embarrassing to put down the management fad that type of book, unless you had pretty good research to back it.

DAN MCGINN: So you take some credit for this?

SCOTT ADAMS: I do in the sense that anything which is marketable, something that by its nature is easy to make fun of. Human nature is such that you want to avoid it. You don’t want to be the person that gets mocked. So I heard lots of anecdotal reports from people, who would say, my boss started to say something that was ridiculous, kind of management fad talk, buzz words, and stopped himself and said, OK, this sounds like it came out of the Dilbert comic.

And then kind of reset and started talking English again. So I do know that the fear of being the target of humor, and it’s very real, because if you get too crazy, you’re going to have a Dilbert comic slipped under your door or emailed to you anonymously. People want to avoid that. So yeah, it’s a little bit of a control on the worst of the management fad excesses, I think.

DAN MCGINN: Well Scott, thanks for joining us today.

SCOTT ADAMS: Thanks so much for having me.

DAN MCGINN: That was Scott Adams. The book is How to Fail at Everything and Still Win Big. For more, visit hbr.org.